EA020332B1 - Аналоги гетероариламидов - Google Patents

Info

Publication number

EA020332B1

EA020332B1 EA200971085A EA200971085A EA020332B1 EA 020332 B1 EA020332 B1 EA 020332B1 EA 200971085 A EA200971085 A EA 200971085A EA 200971085 A EA200971085 A EA 200971085A EA 020332 B1 EA020332 B1 EA 020332B1

Authority

EA

Eurasian Patent Office

Prior art keywords

pyrimidin

methyl

indole

carboxamide

chloro

Prior art date

2007-08-10

Links

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• -1 Heteroaryl amide Chemical class 0.000 title claims abstract description 115
• 150000001875 compounds Chemical class 0.000 claims abstract description 184
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• 229910052700 potassium Inorganic materials 0.000 claims description 34
• 150000003839 salts Chemical class 0.000 claims description 33
• 125000004432 carbon atom Chemical group C* 0.000 claims description 29
• 102100037602 P2X purinoceptor 7 Human genes 0.000 claims description 28
• 101710189965 P2X purinoceptor 7 Proteins 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 150000002367 halogens Chemical group 0.000 claims description 24
• 239000002253 acid Substances 0.000 claims description 22
• 229910052799 carbon Inorganic materials 0.000 claims description 22
• 125000004429 atom Chemical group 0.000 claims description 21
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 21
• 125000002947 alkylene group Chemical group 0.000 claims description 18
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 17
• AINBWHVBVYQQAZ-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-ylindole-3-carboxylic acid Chemical compound C12=CC=CC(Cl)=C2C(C(=O)O)=CN1C1=NC=CC=N1 AINBWHVBVYQQAZ-UHFFFAOYSA-N 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 14
• 239000001257 hydrogen Substances 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 150000001408 amides Chemical class 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
• 125000002757 morpholinyl group Chemical group 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• QKSVJBHORLUNPE-UHFFFAOYSA-N 4-chloro-n-(2-phenylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CC=CC=1C(CCC)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 QKSVJBHORLUNPE-UHFFFAOYSA-N 0.000 claims description 2
• OYPGSBLIRKBVFP-UHFFFAOYSA-N 4-chloro-n-(4-methyl-2-phenylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CC=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 OYPGSBLIRKBVFP-UHFFFAOYSA-N 0.000 claims description 2
• QNCAVWZEJVXGSL-UHFFFAOYSA-N 4-chloro-n-(cycloheptylmethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1CCCCCC1 QNCAVWZEJVXGSL-UHFFFAOYSA-N 0.000 claims description 2
• FKCPUVYYGVELQN-UHFFFAOYSA-N 4-chloro-n-[4-methyl-2-(4-methylphenyl)pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FKCPUVYYGVELQN-UHFFFAOYSA-N 0.000 claims description 2
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• MUCNGXXFDVORKK-UHFFFAOYSA-N n-[2-(1-adamantyl)ethyl]-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(C(=O)NCCC23CC4CC(CC(C4)C2)C3)C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 MUCNGXXFDVORKK-UHFFFAOYSA-N 0.000 claims description 2
• LSGKMZLPZFPAIN-UHFFFAOYSA-N 1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 claims 2
• WBEHRSGSQRLQIT-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C12=CC=CC(Cl)=C2C(C(=O)N)=CN1C1=NC=CC=N1 WBEHRSGSQRLQIT-UHFFFAOYSA-N 0.000 claims 2
• JCSUYDVTWQJBCI-UHFFFAOYSA-N 1-(3-ethylpyrazin-2-yl)-n-[(1-pyridin-3-ylcyclohexyl)methyl]indole-3-carboxamide Chemical compound CCC1=NC=CN=C1N1C2=CC=CC=C2C(C(=O)NCC2(CCCCC2)C=2C=NC=CC=2)=C1 JCSUYDVTWQJBCI-UHFFFAOYSA-N 0.000 claims 1
• VWVZFHRDLPHBEG-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfanylbenzene Chemical group CSC1=CC=C(CCl)C=C1 VWVZFHRDLPHBEG-UHFFFAOYSA-N 0.000 claims 1
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
• FTKQORPRCLRPNX-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-yl-n-(3,3,5-trimethylcyclohexyl)indole-3-carboxamide Chemical compound C1C(C)(C)CC(C)CC1NC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FTKQORPRCLRPNX-UHFFFAOYSA-N 0.000 claims 1
• LRSPAPPWXYSXKT-UHFFFAOYSA-N 4-chloro-n-(2,3-diphenylpropyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)CC1=CC=CC=C1 LRSPAPPWXYSXKT-UHFFFAOYSA-N 0.000 claims 1
• WSPSZBVPJYACII-UHFFFAOYSA-N 4-chloro-n-(2-cyclohexyl-2-phenylethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)C1CCCCC1 WSPSZBVPJYACII-UHFFFAOYSA-N 0.000 claims 1
• RGVNVQZTKWHPNU-UHFFFAOYSA-N 4-chloro-n-(3-cyclopentyl-2-phenylpropyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)CC1CCCC1 RGVNVQZTKWHPNU-UHFFFAOYSA-N 0.000 claims 1
• NQIVGAXWGWVAGP-UHFFFAOYSA-N 4-chloro-n-(3-methylbutyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C12=CC=CC(Cl)=C2C(C(=O)NCCC(C)C)=CN1C1=NC=CC=N1 NQIVGAXWGWVAGP-UHFFFAOYSA-N 0.000 claims 1
• JNXFOEOZSYOZCN-UHFFFAOYSA-N 4-chloro-n-(3-phenylbutyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CC=CC=1C(C)CCNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 JNXFOEOZSYOZCN-UHFFFAOYSA-N 0.000 claims 1
• KQVGATDURWAKBQ-UHFFFAOYSA-N 4-chloro-n-(4-methyl-2-pyridin-3-ylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CN=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 KQVGATDURWAKBQ-UHFFFAOYSA-N 0.000 claims 1
• YPHBXMYPYMXXKK-UHFFFAOYSA-N 4-chloro-n-(4-phenylbutyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCCCCC1=CC=CC=C1 YPHBXMYPYMXXKK-UHFFFAOYSA-N 0.000 claims 1
• QHXNCWYVURIMHA-UHFFFAOYSA-N 4-chloro-n-[(1-hydroxycyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(Cl)=C2C=1C(=O)NCC1(O)CCCCC1 QHXNCWYVURIMHA-UHFFFAOYSA-N 0.000 claims 1
• MJSYWSCNWAHYJT-UHFFFAOYSA-N 4-chloro-n-[(1-hydroxycyclopentyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(Cl)=C2C=1C(=O)NCC1(O)CCCC1 MJSYWSCNWAHYJT-UHFFFAOYSA-N 0.000 claims 1
• NDLYAXIBRQFGQO-UHFFFAOYSA-N 4-chloro-n-[(4-hydroxythian-4-yl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC(Cl)=C2C=1C(=O)NCC1(O)CCSCC1 NDLYAXIBRQFGQO-UHFFFAOYSA-N 0.000 claims 1
• LYJDGLXLBJVRCJ-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)-4-methylpentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 LYJDGLXLBJVRCJ-UHFFFAOYSA-N 0.000 claims 1
• FSSJSUBFNKMDTL-UHFFFAOYSA-N 4-chloro-n-[2-(4-chlorophenyl)pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CCC)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FSSJSUBFNKMDTL-UHFFFAOYSA-N 0.000 claims 1
• FAURIVHGMPPVLE-UHFFFAOYSA-N 4-chloro-n-[4-methyl-2-[4-(trifluoromethyl)phenyl]pentyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FAURIVHGMPPVLE-UHFFFAOYSA-N 0.000 claims 1
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
• AFWMMWSWXVYLDZ-UHFFFAOYSA-N n-(1-adamantylmethyl)-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 AFWMMWSWXVYLDZ-UHFFFAOYSA-N 0.000 claims 1
• NCRXZRNQZWAQQE-UHFFFAOYSA-N n-(1-adamantylmethyl)-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(C(=O)NCC23CC4CC(CC(C4)C2)C3)C=2C(C)=CC=CC=2N1C1=NC=CC=N1 NCRXZRNQZWAQQE-UHFFFAOYSA-N 0.000 claims 1
• GXQNBGUOACJYPR-UHFFFAOYSA-N n-(2-adamantyl)-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(C(=O)NC2C3CC4CC(C3)CC2C4)C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 GXQNBGUOACJYPR-UHFFFAOYSA-N 0.000 claims 1
• KAKVGAOZPOYJDQ-UHFFFAOYSA-N n-[(1-morpholin-4-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC=C2C=1C(=O)NCC1(N2CCOCC2)CCCCC1 KAKVGAOZPOYJDQ-UHFFFAOYSA-N 0.000 claims 1
• YYRCJXPQPPOVIB-UHFFFAOYSA-N n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1N(C=2N=CC=CN=2)C2=CC=CC=C2C=1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 YYRCJXPQPPOVIB-UHFFFAOYSA-N 0.000 claims 1
• CSLSUGNOOSSJQR-UHFFFAOYSA-N n-[2-(2-bromophenyl)ethyl]-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCCC1=CC=CC=C1Br CSLSUGNOOSSJQR-UHFFFAOYSA-N 0.000 claims 1
• PSJGDAHXFKXRLX-UHFFFAOYSA-N n-[2-(4-bromophenyl)ethyl]-4-chloro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCCC1=CC=C(Br)C=C1 PSJGDAHXFKXRLX-UHFFFAOYSA-N 0.000 claims 1
• JUPFTIKYNNMMRM-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-morpholin-4-ylethyl]-1-pyrimidin-2-yl-4-(trifluoromethyl)indole-3-carboxamide Chemical compound C1=2C(C(F)(F)F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCOCC1 JUPFTIKYNNMMRM-UHFFFAOYSA-N 0.000 claims 1
• NMZOKSLIMKWCSU-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-4-fluoro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCCCC1 NMZOKSLIMKWCSU-UHFFFAOYSA-N 0.000 claims 1
• GCXBEEBQOLYVLA-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCCCC1 GCXBEEBQOLYVLA-UHFFFAOYSA-N 0.000 claims 1
• SUYBFJWMWRJOCU-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-4-methylpentyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CC(C)C)CNC(=O)C(C1=C(C)C=CC=C11)=CN1C1=NC=CC=N1 SUYBFJWMWRJOCU-UHFFFAOYSA-N 0.000 claims 1
• UYOZVFBAAGNPAH-UHFFFAOYSA-N n-[2-(6-methoxypyridin-3-yl)-2-piperidin-1-ylethyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=NC(OC)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(C)C=CC=C11)=CN1C1=NC=CC=N1 UYOZVFBAAGNPAH-UHFFFAOYSA-N 0.000 claims 1
• KKGOARLCUKPGGM-UHFFFAOYSA-N n-[[1-(4-chloro-3-fluorophenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(Cl)C(F)=CC(C2(CNC(=O)C=3C4=CC=CC=C4N(C=4N=CC=CN=4)C=3)CCCCC2)=C1 KKGOARLCUKPGGM-UHFFFAOYSA-N 0.000 claims 1
• OXYXAQHHQONHMX-UHFFFAOYSA-N n-[[1-(4-chlorophenyl)cyclohexyl]methyl]-4-fluoro-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=CC(Cl)=CC=2)CCCCC1 OXYXAQHHQONHMX-UHFFFAOYSA-N 0.000 claims 1
• JZVQKMGKZYXCCJ-UHFFFAOYSA-N n-[[1-(4-methoxyphenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 JZVQKMGKZYXCCJ-UHFFFAOYSA-N 0.000 claims 1
• ITLQNYHTRGSTRM-UHFFFAOYSA-N n-[[1-(4-methoxyphenyl)cyclohexyl]methyl]-4-methyl-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1(CNC(=O)C=2C3=C(C)C=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 ITLQNYHTRGSTRM-UHFFFAOYSA-N 0.000 claims 1
• JBBHYKYPYOHBHL-UHFFFAOYSA-N n-[[1-(4-methylphenyl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=CC(C)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 JBBHYKYPYOHBHL-UHFFFAOYSA-N 0.000 claims 1
• XTFXNXJNPJKQNQ-UHFFFAOYSA-N n-[[1-(6-methylpyridin-3-yl)cyclohexyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=NC(C)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 XTFXNXJNPJKQNQ-UHFFFAOYSA-N 0.000 claims 1
• 230000008520 organization Effects 0.000 claims 1
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